Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes

Cyclic alkyl(amino)carbene‐stabilized (cyano)hydroboryl anions were synthesized by deprotonation of (cyano)dihydroborane precursors. While they display boron‐centered nucleophilic reactivity towards organohalides, generating fully unsymmetrically substituted cyano(hydro)organoboranes, they show cyan...

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Autores principales: Gärtner, Annalena, Marek, Matthäus, Arrowsmith, Merle, Auerhammer, Dominic, Radacki, Krzysztof, Prieschl, Dominic, Dewhurst, Rian D., Braunschweig, Holger
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8362087/
https://www.ncbi.nlm.nih.gov/pubmed/33830542
http://dx.doi.org/10.1002/chem.202101025
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author Gärtner, Annalena
Marek, Matthäus
Arrowsmith, Merle
Auerhammer, Dominic
Radacki, Krzysztof
Prieschl, Dominic
Dewhurst, Rian D.
Braunschweig, Holger
author_facet Gärtner, Annalena
Marek, Matthäus
Arrowsmith, Merle
Auerhammer, Dominic
Radacki, Krzysztof
Prieschl, Dominic
Dewhurst, Rian D.
Braunschweig, Holger
author_sort Gärtner, Annalena
collection PubMed
description Cyclic alkyl(amino)carbene‐stabilized (cyano)hydroboryl anions were synthesized by deprotonation of (cyano)dihydroborane precursors. While they display boron‐centered nucleophilic reactivity towards organohalides, generating fully unsymmetrically substituted cyano(hydro)organoboranes, they show cyano‐nitrogen‐centered nucleophilic reactivity towards haloboranes, resulting in the formation of hitherto unknown linear 2‐aza‐1,4‐diborabutatrienes.
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spelling pubmed-83620872021-08-17 Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes Gärtner, Annalena Marek, Matthäus Arrowsmith, Merle Auerhammer, Dominic Radacki, Krzysztof Prieschl, Dominic Dewhurst, Rian D. Braunschweig, Holger Chemistry Full Papers Cyclic alkyl(amino)carbene‐stabilized (cyano)hydroboryl anions were synthesized by deprotonation of (cyano)dihydroborane precursors. While they display boron‐centered nucleophilic reactivity towards organohalides, generating fully unsymmetrically substituted cyano(hydro)organoboranes, they show cyano‐nitrogen‐centered nucleophilic reactivity towards haloboranes, resulting in the formation of hitherto unknown linear 2‐aza‐1,4‐diborabutatrienes. John Wiley and Sons Inc. 2021-05-26 2021-07-02 /pmc/articles/PMC8362087/ /pubmed/33830542 http://dx.doi.org/10.1002/chem.202101025 Text en © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Gärtner, Annalena
Marek, Matthäus
Arrowsmith, Merle
Auerhammer, Dominic
Radacki, Krzysztof
Prieschl, Dominic
Dewhurst, Rian D.
Braunschweig, Holger
Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes
title Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes
title_full Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes
title_fullStr Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes
title_full_unstemmed Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes
title_short Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes
title_sort boron‐ versus nitrogen‐centered nucleophilic reactivity of (cyano)hydroboryl anions: synthesis of cyano(hydro)organoboranes and 2‐aza‐1,4‐diborabutatrienes
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8362087/
https://www.ncbi.nlm.nih.gov/pubmed/33830542
http://dx.doi.org/10.1002/chem.202101025
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